Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

Jingjing Wu; Robin M. Bär; Lin Guo; Adam Noble; Varinder K. Aggarwal

doi:10.1002/anie.201910051

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

Jingjing Wu
, Robin M. Bär
, Lin Guo
, Adam Noble
, Varinder K. Aggarwal^*

^*Corresponding author for this work

University of Bristol

Research output: Contribution to journal › Article › peer-review

132 Scopus citations

Abstract

A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2-iodophenyl-thionocarbonate enables a novel Barton–McCombie-type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.

Original language	English
Pages (from-to)	18830-18834
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	58
Issue number	52
DOIs	https://doi.org/10.1002/anie.201910051
State	Published - 19 Dec 2019
Externally published	Yes

Keywords

boronic esters
borylation
deoxygenation
photochemistry
radical reactions

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10.1002/anie.201910051

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@article{5a83418a92294b1bacfabd2df31626ad,

title = "Photoinduced Deoxygenative Borylations of Aliphatic Alcohols",

abstract = "A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2-iodophenyl-thionocarbonate enables a novel Barton–McCombie-type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.",

keywords = "boronic esters, borylation, deoxygenation, photochemistry, radical reactions",

author = "Jingjing Wu and B{\"a}r, \{Robin M.\} and Lin Guo and Adam Noble and Aggarwal, \{Varinder K.\}",

note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH \& Co. KGaA, Weinheim",

year = "2019",

month = dec,

day = "19",

doi = "10.1002/anie.201910051",

language = "英语",

volume = "58",

pages = "18830--18834",

journal = "Angewandte Chemie - International Edition",

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TY - JOUR

T1 - Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

AU - Wu, Jingjing

AU - Bär, Robin M.

AU - Guo, Lin

AU - Noble, Adam

AU - Aggarwal, Varinder K.

PY - 2019/12/19

Y1 - 2019/12/19

N2 - A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2-iodophenyl-thionocarbonate enables a novel Barton–McCombie-type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.

AB - A photochemical method for converting aliphatic alcohols into boronic esters is described. Preactivation of the alcohol as a 2-iodophenyl-thionocarbonate enables a novel Barton–McCombie-type radical deoxygenation that proceeds efficiently with visible light irradiation and without the requirement for a photocatalyst, a radical initiator, or tin or silicon hydrides. The resultant alkyl radical is intercepted by bis(catecholato)diboron, furnishing boronic esters from a diverse range of structurally complex alcohols.

KW - boronic esters

KW - borylation

KW - deoxygenation

KW - photochemistry

KW - radical reactions

UR - https://www.scopus.com/pages/publications/85075156839

U2 - 10.1002/anie.201910051

DO - 10.1002/anie.201910051

M3 - 文章

C2 - 31613033

AN - SCOPUS:85075156839

SN - 1433-7851

VL - 58

SP - 18830

EP - 18834

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 52

ER -

Photoinduced Deoxygenative Borylations of Aliphatic Alcohols

Abstract

Keywords

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